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Chemical Structure| 161596-47-0 Chemical Structure| 161596-47-0
Chemical Structure| 161596-47-0

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CAS No.: 161596-47-0

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Product Details of [ 161596-47-0 ]

CAS No. :161596-47-0
Formula : C11H9NO3
M.W : 203.19
SMILES Code : O=C1N(C[C@@H]2OC2)C(C3=C1C=CC=C3)=O
MDL No. :MFCD04973350
InChI Key :DUILGEYLVHGSEE-ZETCQYMHSA-N
Pubchem ID :719412

Safety of [ 161596-47-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Application In Synthesis [ 161596-47-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 161596-47-0 ]

[ 161596-47-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 161596-47-0 ]
  • [ 438056-69-0 ]
  • [ 446292-07-5 ]
YieldReaction ConditionsOperation in experiment
92% at 65 - 70℃; for 32 h; 4-(4-aminophenyl)morpholinone 100 gm, 0.5202 moles and (S)-(+)glycidyl phthalimide 106.6 gm ( 0.5246 moles) was charged to the mixture of, methanol and water 1000 ml (9: 1) and heated to 65°C-70°C. Continued stirring for next 20 hrs at 65°C-70°C. Add second lot of S)-(+)glycidyl phthalimide 10.6 gm (0.05246 moles) and 200 ml (9: 1) methanol water mixture and stir for next 12 hrs. Cooled the reaction mass to 25°C-30°C and filter the slurry on Buckner funnel, suck dried well. Wet cake washed with 100 ml mixture of methanol and water (9: 1). The solid obtained was dried at 50°C to 55°C to get 190 gm compound of Formula-3 as dry material. Yield-92percent
92% for 10 h; Reflux Add 4-(4-aminophenyl)morphin-3-one (192.2 g, 1 mol) to a 1000 ml three-necked flask,2-(2-chloroethoxy)propane(203.2 g, 1 mol), 790 ml of ethanol, stirring was started, the temperature was raised to reflux, and the TLC was detected. It was found that the starting material disappeared after 10 hours of reaction, and the reaction was completed and lowered to room temperature. After suction filtration, 100 ml of ethanol was washed three times, and the compound (4) was dried to obtain 363.78 g, the yield was 92percent, and the HPLC detection was 98.67percent.
89.7% for 14 h; Reflux A mixture of 5.68 g(27.9 mmol) of compound V was added compound VI 5.35 g (27.9 mmol) was suspended in 140 ml of 1/9 water - ethanol, stirring reflux for 14 hours, cooled to 20 °C, filter, filter the filter cake with ethanol 3 times. 65-70 °C under reduced pressure, to obtain 9.9 g of the compound of the formula (I) (yield: 89.7percent ) HPLC content 98.5percent (normalization).
87.5% at 25℃; for 24 h; Reflux In a four neck round bottom flask charged Isopropyl alcohol (135 ml), 4-(4-aminophenyl) morpholin-3-one (10 g), 2-[(2s)-oxiran-2yl methyl]-lH-isoindole-l,3(2H) dione ((11.6 g) and water (15 ml) at 25 to 30°C. Slowly heated the reaction mixture to reflux and maintained for 24 h at reflux temperature. Reaction mass is cooled to 25 to 30°C after completion of the reaction. Reaction mass then maintained at 25 to 30°C for 30 minutes. Finally obtained solid is filtered off and washed by isopropyl alcohol (25 ml) Yield 87.5percent
87.5% for 24 h; Reflux To a 2 litre 4 neck RBF, charge Methanol (1500 ml), 4-(4-aminophenyl)-3-morpholinone Compound (VI), (100 gms), (S)-Glycidyl Phthalimide Compound (V), (127 gms). Reflux the reaction mass for 24 hrs. Cool the reaction mass at 25-30°C and filter. Wash the residue with Methanol (50 ml). Dry the solid at 45-50°C under vacuum. Dry Wt: 180 gms (Theoretical yield: 87.50percent); Purity: 98.20percent
82.6% Reflux A suspension of 4-(4-aminophenyl)morpholin-3-one (100 gm) and 2-[(2S)-oxiran-2-ylmethyl}-1H-isoindole-1,3(2H)-dione (116.2 gm) in isopropyl alcohol and water mixture (l700ml :300 ml) is refluxed for 25-30 h. The precipitated solid is filtered off, washed with isopropyl alcohol (100 ml) to obtain solid, which is then dried under vacuum at 50 to 55 °C for 4 to5 hr to obtain 2-[(2R)-2-hydroxy-3-[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]-1 H-isoindole-1,3(2H)-dione. [Yield = 170 gm (82.6percent); Purity (H PLC) = 95.0 percent]
82.6% Reflux A suspension of 4-(4-aminophenyl)morpholin-3-one (100 gm) and 2-[(2S)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (116.2 gm) in isopropyl alcohol and water mixture (1700 ml:300 ml) is refluxed for 25-30 h.
The precipitated solid is filtered off, washed with isopropyl alcohol (100 ml) to obtain solid, which is then dried under vacuum at 50 to 55° C. for 4 to 5 hr to obtain 2-[(2R)-2-hydroxy-3-[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]-1H-isoindole-1,3(2H)-dione. [Yield=170 gm (82.6percent); Purity (HPLC)=95.0percent]
82.7% at 0 - 60℃; for 20 h; Large scale This example relates to the preparation of 2-{(fl)-2-hydroxy-3-[4-(3-oxo- morpholine-4-yl)-phenylamino]-propyl}isoindol-1 ,3-dione, step a) of the process. 10.0 kg of 4-(4-aminophenyl)morpholine-3-one, 13.0 kg of (S)-(+)-N-(2,3- epoxypropyl)phthalimide and 170 kg of methanol are loaded into a reactor as a single solvent. The mass is heated to around 60 °C and maintained at this temperature for 20 hours, then cooled to 0-10 °C. There is precipitation of the desired product, which is filtered and washed with 30.0 kg of methanol. The product obtained is oven-dried, obtaining 17.0 kg of the desired compound (III), with a reaction yield equal to 82.7percent.
81.4% at 20 - 60℃; for 36 h; 1173 g of 2-[(2S)-2-oxiranylmethyl]-1H-isoindole-1,3(2H)dione (II) and 4-(4-aminophenyl)-3-morpholinone (III) are mixed at 20° C. with 6.7 l of water and 14.4 l of ethanol.
The suspension is heated to 58 to 60° C., and the resulting solution is stirred for 36 hours.
After 2 hours, 5 g of crystalline 2-((2R)-2-hydroxy-3-[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (V) are added to the reaction mixture, after which the product starts to crystallize.
After cooling to 26° C., the precipitated reaction product is filtered off with suction, washed with ethanol and then dried.
Yield: 1522 g; equivalent to 81.4percent of theory.
Melting point: 215° C.
80.68% at 80℃; for 9 h; 238.50 g (1.174 mol) of 2-[(2S)-2-oxiranylmethyl]-1 H-isoindole-1 , 3(2H)-dione (I), 150 g (0.781 mol) of 4-(4-amino phenyl)-3-morpholinone and 3L of ethanol were charged in a 5L flask and the reaction mass was heated at 80 °C for 9 hours. Afterwards the reaction mass was cooled down to 30 °C, and the resulting solid was filtered off and dried under vacuum at 70 °C.Yield: 249 g. Molar yield: 80.68percent. HPLC purity 96.90percent. M.P.: 214 °C. Specific Optical Rotation (S.O.R.): [a ]D25 = +6.24° (c = 1 ,DMSO)
75.4% With water In ethanol at 60℃; for 36 h; Industry scale A suspension of (S) -2- (oxiran-2-ylmethyl) isoindoline-1, 3-dione (4.5kg, 1.22eq) and 4- (4-aminophenyl) morpholin-3-one (3.286kg , 17.088 mol) in ethanol/water (42L/16kg), was heated at 60 0C for 36 hours. It was further cooled to room temperature, the precipitate was filtered, and dried in vacuum. An amount of 5.1 kg of the product was obtained (Yield 75,4percent).
203 g at 80℃; for 8 h; To 100 gm (0.5208 moles) of 4-(4-Aminophenyl) morpholin-3-one (III) in 2500 ml purified water, 185 gm (0.9104 moles) of (S)- Glycidyl Phthalimide (IV) and 1000ml purified water0 was charged and the reaction mixture was heated to 80 °C for 8 hours. The precipitated products was filtered and washed with purified water. The product was dried under vacuum at 60°C to 65°C for 24 hours. Dried weight = 203 gm

References: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5900 - 5908.
[2] Patent: WO2018/127762, 2018, A1, . Location in patent: Page/Page column 12.
[3] Patent: CN108164519, 2018, A, . Location in patent: Paragraph 0014; 0015; 0016; 0017.
[4] Patent: CN106588905, 2017, A, . Location in patent: Paragraph 0044; 0046-0047.
[5] Patent: WO2014/102820, 2014, A2, . Location in patent: Paragraph 047.
[6] Patent: WO2016/199027, 2016, A1, . Location in patent: Page/Page column 18.
[7] Patent: WO2013/121436, 2013, A2, . Location in patent: Page/Page column 26.
[8] Patent: US2015/11756, 2015, A1, . Location in patent: Paragraph 0117.
[9] Patent: WO2015/198259, 2015, A1, . Location in patent: Page/Page column 6.
[10] Patent: US2005/182055, 2005, A1, . Location in patent: Page/Page column 1; 3.
[11] Patent: WO2005/68456, 2005, A1, . Location in patent: Page/Page column 7.
[12] Patent: WO2013/53739, 2013, A1, . Location in patent: Page/Page column 31.
[13] Patent: WO2011/12321, 2011, A1, . Location in patent: Page/Page column 31.
[14] Patent: WO2013/98833, 2013, A2, . Location in patent: Page/Page column 41.
[15] Patent: US2014/378682, 2014, A1, . Location in patent: Paragraph 0209; 0210.
[16] Patent: WO2016/30669, 2016, A1, . Location in patent: Page/Page column 28.
  • 2
  • [ 161596-47-0 ]
  • [ 446292-07-5 ]
YieldReaction ConditionsOperation in experiment
75% for 20 h; Reflux Example 3: (2R)-2-Hydroxy-3-[4-(3-oxo-4-morpholinyl)phenyI]aminopropyl-lH-isoindol- l,3(2H)-dione, the compound of formula III(S)-2-(Phthalimidomethyl)oxirane (12.0 g; 0.06 mol) and N-(4-aminophenyl)- morpholinone (10.0 g; 0.05 mol) were charged into a flask and methanol (200 ml) and water (20 ml) were added. The mixture was heated up to boil and refluxed for 20 hours. The white suspension was cooled to the temperature of 15°C, stirred for 1 hour, aspirated and washed with methanol (20 ml) at the temperature of 15°C.The thoroughly aspirated product was dried in a vacuum drier at a temperature up to 60°C. 15.5g (75 percent of theory) of (2R)-2-hydroxy-3-[4-(3-oxo-4-morpholinyl)phenyl]aminopropyl- l H-isoindol- l ,3(2H)-dione with the isomeric purity of 99.0percent were obtained.
References: [1] Patent: WO2012/41263, 2012, A2, . Location in patent: Page/Page column 10.
 

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